If L or Grand L, I think you need a new trailer and tow vehicle, especially with the distances you'll be trailering. Many have said these things already, but here's my experience:
2006 F-150 SuperCrew 4X4, camper top,, 5.4 Triton with stuff in the bed like chain saws, as tow vehicle:
L3800 as tractor, dual axle trailer rated at 7,500 lbs. Tractor with 800 lbs loader, tooth bar, 550 lb box blade, loaded rear R4's, chains and binders - pulled on truck scale at local Love's travel station. 12,850 lbs.
Not sure what my truck weighs by itself, but the tractor and implements, etc, combined with the trailer weight itself (with a tool box filled with stuff on the tongue), had to be getting close to the trailer rating.
My truck would pull this alright, but I wouldn't be the fast guy on the road and I certainly wouldn't tow this without having trailer brakes. They are a must for this kind of load IMO.
Also, to get the load proportioned well with good tongue weight, my bucket would have to sit on the tool box on the tongue of the trailer and I couldn't turn too sharp for fear of putting a tooth through my tailgate. This load with Box Blade would take about the rest of the 16' trailer length and have the ramps folded up with not much room to spare. When I had a bush hog on, I had to slide ramps to the outermost setting and still couldn't fold them even to vertical. I had to chain them hanging out to some degree. The bush hog would stick off the back of the trailer.
In fact, now that I have the BX-2370, this 16' trailer a better match, but even still this tractor with a bush hog will still be a tight squeeze, although more comfortable than the
L3800.
My advice to your wife :laughing:: you need a 3/4 ton or larger diesel truck, with a 20' tandem axle dovetail or tilt trailer (with brakes!) to adequately handle your tractor choice and be safe and comfortable towing so much to your property. Rear finish mower's hang off the back nearly as much as bush hogs.